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Robbie Keane and 5 Liverpool Regrets in the Transfer Market

Max MuntonOct 9, 2014

Robbie Keane, the player who as a child growing up in Ireland, infamously supported every club he went on to play for, signed for Liverpool from Tottenham in a £20.3 million deal in July 2008.

Keane signed a four-year deal at Anfield off the back of some shady negotiations with Liverpool, as per Andy Hunter of The Guardian, that could have got the club into hot water had they not made a donation to the Tottenham Hotspur Foundation.

His start at Anfield was slow to say the least, taking until October to score his first goal for the club, and by January, he had only scored seven in 28 appearances.

Keane was having a miserable time on Merseyside, but Tottenham came back in with an bid to take him back to White Hart Lane during the January transfer window. Liverpool accepted and Keane's brief cameo in a red shirt was over.

We've selected five more Liverpool regrets in the transfer market here for you to wince over. Let us know in the comments section below any more bad moves that come to mind. Just don't say Mario Balotelli, unless you've got a heart of stone.

Joe Cole

1 of 5

In 2010's summer of madness for the club under former owners Tom Hicks and George Gillett, Roy Hodgson was appointed Liverpool manager.

He proceeded to bring in a number of players who arguably didn't even belong in the Premier League, never mind at a club with such big ambitions as Liverpool.

One of those players was England midfielder Joe Cole, available on a free transfer after his contract at Chelsea expired.

After being sent off on his debut against Arsenal, Cole's fitness plummeted, and he never got back to the highs he showcased at Stamford Bridge.

He made 42 lacklustre appearances for Liverpool before moving to French side Lille on loan. He eventually secured a permanent move to West Ham United.

Paul Konchesky

2 of 5

Paul Konchesky is a name synonymous with Hodgson's dark six months at Liverpool.

Signed on a four-year contract, Konchesky instantly looked a class below the club, quickly becoming a villain when his mum made an attack on Liverpool fans on her Facebook account, as per Dominic King of the Daily Mail.

When he was taken off during a depressing defeat to Wolves at Anfield, the substitution was welcomed by an ironic round of cheers from the Kop.

After a loan spell at Nottingham Forest, he was let go to Leicester City in 2011. He will make his Anfield return this season for the Foxes when the sides meet in the Premier League on New Year's Day.

Andy Carroll

3 of 5

January 31, 2011: the fateful, whirlwind day in which Fernando Torres kissed goodbye his career in a £50 million switch to Chelsea, prompting Liverpool to launch a £35 million bid for Newcastle United striker Andy Carroll.

Barely proven in the Premier League, Carroll was eyed by the club's director of football, Damien Comolli, for his height and strength to boost Liverpool upfront.

A week previously, the Reds had signed Ajax and Uruguay international Luis Suarez. The story of the two forwards could not be further apart—Carroll scoring just 11 goals in 58 appearances for the club before West Ham ended his nightmare stay on Merseyside with a £15 million bid following a season on loan at Upton Park.

He did provide one moment of magic, however, when he scored a late winner against Everton in the 2012 FA Cup semi-final at Wembley to book Liverpool's place in the final.

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Salif Diao

4 of 5

Salif Diao was a longstanding servant of Liverpool, though you wouldn't have known it, having been signed by Gerard Houllier on a five-year deal in 2002.

Clocking up just 61 underwhelming appearances both in defence and midfield during that time, Diao must go down as an expensive mistake in the club's transfer history, though his wages were subsidised by loan spells at Birmingham City, Portsmouth and Stoke City between 2005 and 2007.

Oussama Assaidi

5 of 5

Mystery surrounded Liverpool's signing of Moroccan international winger Oussama Assaidi in 2012.

The club were in transition at the time with managers coming and going and other staff at the club having their two cents' worth.

But a £2.4 million deal was agreed with Dutch side Heerenveen for his services and the now-26-year-old made 12 appearances in all competitions for Liverpool in 2012-13.

That looks to have been the end of things as far as Assaidi and Liverpool are concerned, having spent 2013-14 on loan at Stoke City and again this season, yet he remains on the books at Anfield.

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